Bone collagen cross-links: an efficient one-pot synthesis of (+)-pyridinoline and (+)-dexoypyridinoline |
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| Institution: | 1. Division of Fuel Cell & Battery, Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, PR China;2. University of the Chinese Academy of Sciences, Beijing 100039, PR China |
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| Abstract: | A one-pot reaction of (2S,5R)-(?)-tert-butyl-(2-tert-butoxycarbonyl)amino]-5-hydroxy-6-aminohexanoate 2b or (S)-(?)-tert-butyl-(2-tert-butoxycarbonyl)amino]-6-aminohexanoate 2c with (S)-(?)-tert-butyl-6-bromo-bis-(2-tert-butoxycarbonyl)amino]-5-oxohexanoate 5 in the presence of K2CO3 in MeCN–MeOH followed by hydrolysis gave bone collagen cross-links, (+)-Pyd 1b or (+)-Dpd 1c, in 42–48% yield, respectively. |
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